21. Heathers (1988 – Michael Lehmann)
Heathers is one of the most influential, dark comedy classics of its time. The cutting-edge slang-filled dialogue started a whole new trend in writing that inspired other writers like Joss Whedon. Starring huge 80s stars Winona Ryder and Shannon Doherty, this movie captures the Midwestern high school life of a clique of four attractive, curious, and somewhat audacious girls – three of which are named Heather. It’s been ranked in the top five ‘best high school movie’ lists and received impressive critical acclaim upon its release in 1988.